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Volumn , Issue 9, 2005, Pages 1359-1369

α-lithiated aryloxiranes: Useful reactive intermediates

Author keywords

Asymmetric synthesis; Carbanions; Carbenoids; Epoxides; Lithium

Indexed keywords

CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; OXAZOLINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPYLENE; REAGENT; STILBENE OXIDE; STYRENE;

EID: 20544436122     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868521     Document Type: Review
Times cited : (44)

References (78)
  • 10
    • 5644297285 scopus 로고    scopus 로고
    • Rappoport, Z.; Marek, I., Eds.; John Wiley and Sons: New York, Chap. 18
    • (d) Chemla, P.; Vrancken, E. In The Chemistry of Organolithium Compounds, Vol. 2; Rappoport, Z.; Marek, I., Eds.; John Wiley and Sons: New York, 2004, Chap. 18, 1165-1242.
    • (2004) The Chemistry of Organolithium Compounds , vol.2 , pp. 1165-1242
    • Chemla, P.1    Vrancken, E.2
  • 11
    • 0242475011 scopus 로고    scopus 로고
    • (e) For a special issue on Oxiranyl and Aziridinyl Anions (Florio, S., Ed.), see: Florio, S. Tetrahedron 2003, 59, 9693.
    • (2003) Tetrahedron , vol.59 , pp. 9693
    • Florio, S.1
  • 13
    • 9444294970 scopus 로고    scopus 로고
    • and references therein
    • For a recent paper on the generation of terminal non-stabilized oxiranyllithium species and their trapping with electrophiles, see: Hodgson, D. M.; Reynolds, N. J.; Coote, S. J. Org. Lett. 2004, 6, 4187; and references therein.
    • (2004) Org. Lett. , vol.6 , pp. 4187
    • Hodgson, D.M.1    Reynolds, N.J.2    Coote, S.J.3
  • 25
    • 20544477768 scopus 로고    scopus 로고
    • note
    • (b) For other examples of electrocyclic α-ring-opening involving lithiated oxiranes, see ref. 2d, pp 1210-1218
  • 26
    • 0037463739 scopus 로고    scopus 로고
    • (c) A similar isomerization has been also observed for β-aryl-substituted α-lithiated oxazolinylaziridines, see: Luisi, R.; Capriati, V.; Florio, S.; Ranaldo, R. Tetrahedron Lett. 2003, 44, 2677.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2677
    • Luisi, R.1    Capriati, V.2    Florio, S.3    Ranaldo, R.4
  • 32
    • 0000345527 scopus 로고    scopus 로고
    • Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, Chap. 18.2
    • (c) Fora review, see: Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis, Vol. 2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999, Chap. 18.2.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2
    • Jacobsen, E.N.1    Wu, M.H.2
  • 50
    • 20544469282 scopus 로고    scopus 로고
    • note
    • Less than 1 equiv of TMEDA led to the recovery of starting material and to minor yields of products.
  • 67
    • 0035296971 scopus 로고    scopus 로고
    • (e) For a recent review on the electrophilic nature of carbenoids, see: Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697.
    • (2001) Chem. Rev. , vol.101 , pp. 697
    • Boche, G.1    Lohrenz, J.C.W.2
  • 70
    • 0035965107 scopus 로고    scopus 로고
    • For a recent review on epoxy ketones as versatile building blocks in organic synthesis, see: Lauret, C. Tetrahedron: Asymmetry 2001, 12, 2359.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2359
    • Lauret, C.1
  • 72
    • 9444267537 scopus 로고    scopus 로고
    • Tetrahedron Organic Chemistry Series, Pergamon: Oxford
    • Organolithium: Selectivity for Synthesis, Vol. 23; Clayden, J., Ed.; Tetrahedron Organic Chemistry Series, Pergamon: Oxford, 2002, 28-73.
    • (2002) Organolithium: Selectivity for Synthesis , vol.23 , pp. 28-73
    • Clayden, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.